Jacob Weisberg Was a Web Pioneer. But He Doesn’t Much Care for What Works on the Web Now. Can Slate Recover?

A COUPLE OF years after the Washington Post Co. bought Slate, Mr. Weisberg endeared himself to the staff forever: His contract included a $100,000 bonus if the site had a break-even year, and when it happened, he divided it up among his crew. Neither he nor Mr. Plotz took a share.

When Slate arrived on the scene in 1996, it freaked out establishment media with its bare-bones costs — no paper! No ink! Now the shoe is on the other foot, as Slate is the outlet with high overhead — it pays some of the best writers and editors in the business — while others cruise in with their low-cost or no-cost aggregation.

Watching sites more than a decade younger start up and eat their lunch, if not their prestige, has left a feeling among Slate staffers that they are no longer kings of the Web. Years ago, The Times regularly poached talent from Slate’s ranks — Paul Krugman got his start there, as did Jodi Kantor, Virginia Heffernan and Rob Walker. There have been fewer such departures of late. The failures of the Big Money and Double X sting, but what they may prove most of all is that Mr. Weisberg and his editors aimed too high. Neither spin-off included the distasteful business of “aggregating” headlines from around the Web, or very good SEO, the black arts of traffic-conjuring that are considered un-Slate-y.

“Jacob is an intense and rabid study on any number of topics, and knows a lot about Web strategy and SEO, and there are people he can tap who know more,” said James Ledbetter, the former editor of The Big Money, who is now at Reuters. “But I think it’s a fair question whether the company really has that in its DNA, and has allocated resources appropriately to be able to compete.”

The so-so start of the Slate Group is a rare setback for Mr. Weisberg, who is used to finding success at every station, from Yale, to the Rhodes fellowship, to a Young Turk period at The New Republic in Washington, where he, Michael Lewis and Andrew Sullivan all bought condos in a converted schoolhouse in Adams Morgan that the magazine’s editor nicknamed “The Kindergarten.”

“He was always too hip for D.C. — and gayer than me much of the time,” remembers Mr. Sullivan. “We all knew that Jake would be running the world at some point, and I’m sure he is, somewhere, in ways I do not yet comprehend.”

“He was always a grown-up,” Mr. Lewis said. “But sweaty and ambitious — Jacob was never noticeably so. He was just kind of a bright young thing, but with the mind of a 55-year-old University of Chicago professor.” The only other person in journalism with the same smarts for writing, editing and business, he said, was Columbia J-school dean Nicholas Lemann, and maybe the Aspen Institute’s Walter Isaacson.

With blurbs like that, does Mr. Weisberg’s portfolio measure up? With Big Money and Double X scuttled, the Slate Group includes Slate itself and Foreign Policy magazine — but they are self-sufficient publications with terrific editors of their own. Then there is the Root, comfortable in its niche, and Slate V, a viral video site that hasn’t found much traction. In addition, there is a brand-new business called Social Code that sells Facebook ads. The sense within the company (and shared, a bit more intensely, by his peers outside of it) is that all this is fine, but maybe not a full load for a journalist of Mr. Weisberg’s stature — a guy whose name came up early and often in 2006 as a potential successor to Jim Kelly as the editor of Time.

These days, Mr. Weisberg has taken to bicycling to work, an easy mile-or-two pedal from the immaculate white-hued loft in Tribeca where he lives with his wife, Deborah Needleman. (Ms. Needleman is herself a top-flight editor–of red-hot shelter mag Domino before it folded, and now WSJ.) The night before he showed The Observer around Slate’s new office, Mr. Weisberg had thrown a book party for Tim Wu, the Columbia Law professor and Slate writer, that featured two bars, a seven-woman percussion band and at least eight kinds of raw cow’s milk cheese. “Nice jacket,” Mr. Weisberg told The Observer as he greeted guests near the foyer. “Nice boots,” The Observer replied. (Red Wings. Not the J. Crew ones.) A buoyant Mr. Wu, wearing goggles, took off one shirt and put on another in silver lamé.

Jacob Weisberg looked serene. But is he happy? He’s being asked to re-enter the Internet trenches, after having made it across once already, when the Web was more easily conquered.

“I’m having a great time,” he said the next morning. “I feel really lucky to be in on this revolution. It’s why most of us came to Slate in the first place — to invent a new kind of journalism and build a business around it. Boy, has it taken a long time to do that. But it’s happening. We were ahead of our time, and the world has caught up.”

Mr. Lewis, a lifelong friend, agreed. “I think if Jacob was unhappy,” he said, “he’d be the last to know.”